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Showing 1 to 20 of 31 for “"oxazolidinone"”.
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Synthesis of Bicyclic and Tricyclic Analogues of Oxazolidinone
<p>Oxazolidinones are known as a new class of antibacterial agents. In our group, the 4,5-disubstituted oxazolidinones have been previously identified to exhibit high affinity for the T box antiterminator transcription system. Among those compounds, ANB-22 and ANB-40 emerged to be the lead …
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LIGHT-DRIVEN STRATEGIES FOR THE GENERATION OF N-OXAZOLIDINONE RADICALS AND THE SYNTHESIS OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS
… regioselective addition of novel N-oxazolidinone radicals to arenes and heteroarenes, achieved under both photocatalytic and photocatalyst-free conditions in batch and continuous-flow systems; and (B) the application of the photo-Favorskii rearrangement as a key step in the synthesis …
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Towards the Synthesis of the Unusual Monosaccharides Found in the Shigella sonnei O-Antigen and Analysis of Shigella flexneri 2a Glycoconjugate Vaccine Samples
… as a key oxazolidinone-protected intermediate, which allowed for successful preparation of a FucNAc4N derivative in the form of a 4-azido-βthioglycoside. This was achieved in 10 steps from the commercially available …
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Synthesis of novel heterocyclic α-amino acids
… radical addition with an optically active oxazolidinone acceptor derived from (R)-S-methylcysteine to give syn-adducts. Hydrolysis of the oxazolidinone adducts followed by deprotection afforded the desired amino acids carrying pyrimidine- (thymine, uracil) and purine- (adenine, guanine) …
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Chemical and conformational studies of bacterial cell surface polysaccharide repeating units
… developed by the research group. The key 2,3-oxazolidinone protected intermediate was successfully synthesised in good yields and due to time constraints the final product synthesised was two steps away from the protected FucNAc4N residue. Additional studies were performed on the …
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Synthesis And Á-Stereoselective Sialylation Of Kdn And Late Stage Modification Of Neuraminic Acid Sialosides
… the excellent á-directing ability of the acetyl oxazolidinone, oxazolidinone and carbonate cyclic protections in neuraminic acid and KDN were investigated by mass spectrometry using in-source fragmentation of the corresponding sialyl phosphates. The trends of the onset cone voltages for …
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Design and Synthesis of Benzimidazoles as CDK5 Inhibitors and Progress toward the Total Synthesis of Tubulysin D
… fragments of tubulysin were synthesized. Evans' oxazolidinone chemistry was employed for the stereoselective synthesis of Cbz-beta-homovaline in Tuv fragment. A crystal structure of the Tup fragment was obtained.</p><p> Cyclin dependent kinase 5 (CDK5) is one of the kinases that can …
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New routes to enantioenriched substances through small organic molecules
… from the reaction between a set of acids and an oxazolidinone as the chiral auxiliary. The inter- and intramolecular cycloaddition of in situ-generated keteniminium salts gives bicycles with a good enantioselection. A key intermediate of Iloprost, a chemically stable and biologically active mimic …
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SHAPING ORGANIC SYNTHESIS WITH LIGHT-DRIVEN PROCESSES
… chapter reports two methods for introducing oxazolidinone moieties into heterocycles. The first method employs extremely mild reaction conditions (sodium bicarbonate in water) through an EDA complex pathway. The second method, still to be clarified, involves an aggregation-induced …
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The use of chiral auxiliaries in the synthesis of chemically and biologically important chiral compunds
… synthesised using imidazolidinone and Evans' oxazolidinone chiral auxiliaries (CA). The thesis comprises two parts, which were carried out at the Universities of Cape Town, RSA and University of Michigan in the USA. In part 1, carried out in the Chemistry Department of the University of Cape …
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Hemiaminals : a new chemotype for organocatalysis
… aldehydes is reported. The corresponding oxazolidinone- hydrazides are reduced to their oxazolidinones via a modified E1cB elimination using ethyl bromomalonate and potassium carbonate in acetonitrile. The reactions gave high yields (76-96%) and ees (83-95%) with a good chemoselectivity …
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New methodology for the organocatalysed α-Amination reaction
… was also developed for the aminated products in oxazolidinone form. This methodology is based on Magnus' alkylation / E1CB strategy. The novel contribution here is using ditheyl bromoacetate as an alkylating agent and as a better elimination partner. A range of bis-acetals were synthesised via …
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Gold(I) and Platinum(II)-Catalyzed Hydrofunctionalization of Allenes and Alkenes with Carbon and Nitrogen Nucleophiles
… nucleophiles other than cyclic ureas and 2-oxazolidinone that efficiently undergo hydroamination with 1-alkenes. Various carbamates, arylamines, amide derivatives, sulfur-containing amide derivatives, and α-heteroatom compounds failed to react with 1-octene under gold(I)-catalyzed …
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The synthesis and structural characterisation of novel 4- and 5- membered nitrogen heterocycles derived from azoacetates
… This work resulted in the synthesis of novel oxazolidinone and hydantoin species, also with phenylazo attachments. The final chapter describes the incorporation of a cyanide unit into heterocyclic compounds through intermolecular cyclisations of a range of substituted azoacetates when …
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The development of novel organocatalytic and transition-metal catalysed methodologies for amide bond formation
… adapted to enable the synthesis of corresponding oxazolidinone moieties. The use of transition-metal catalysis has also been employed to facilitate amide bond formation. Utilising silanoate-derived imidate salt species, synthesised from the corresponding nitriles as amide surrogates, a …
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Parallel kinetic resolutions using active esters
… for the common resolving agent 4-isopropyl oxazolidinone is solvent dependant. The discovery and further exploration of a method for synthesising a range of optical pure secondary alcohols from the commercial available (S)-enantiomer of 1- (2-bromo-phenyl)-ethanol is also described. An …
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Synthesis of multicyclic ring systems including an alternate route to Meyers’ lactam derivatives
… diastereoselective construction of chiral fused oxazolidinone lactams by utilising the use of Meyers’ lactamisation methodology. This provided high atroposelection through a central C5 to axial chirality transfer. The aim of this project will be directed towards the design of alternative …
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Antiviral Agents: 3,5-Disubstituted 1,2,4-Oxadiazole Derivatives and Novel Peptidomimetics Containing Hydroxyethyl Isostere and Imidazolidinone Structures
… with amino acids or small peptides to form an oxazolidinone, followed by rearrangement to the target imidazolidinone. A chain elongation on the resulting diol with a second amino acid or peptide fragment provides the novel peptidomimetics containing hydroxyethylene isosteres and imidazolidinone …
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Boron Functionalization of BODIPY Dyes, and Their Evaluation as Bioimaging Agents
… reaction was investigated through the use of an oxazolidinone.
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Enantioselective Synthesis of Drug-like Molecules via Axially-Chiral Intermediates
… lactate derivatives containing achiral oxazolidinones, we hypothesized that a twisted amide enolate featuring a chiral C(O-)-N axis could sufficiently impart stereochemical information and control the selectivity of the reaction. Previous work completed by Kobayashi showed in related …
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